Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P450 2C

Biochemical Pharmacology

Volumn 54, Issue 1, 1997, Pages 33-41

  Hamman, Mitchell A ^a   Thompson, Gary A ^b   Hall, Stephen D ^a,c  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b PROCTER AND GAMBLE COMPANY   (United States)

^c WISHARD MEMORIAL HOSPITAL   (United States)

Author keywords

Cytochrome P450; Enantiomers; Human biotransformation; Ibuprofen; Microsomal oxidation

Indexed keywords

2 HYDROXYIBUPROFEN; 3 HYDROXYIBUPROFEN; CYTOCHROME P450; IBUPROFEN; ISOENZYME; NONSTEROID ANTIINFLAMMATORY AGENT; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; ENANTIOMER; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; HYDROXYLATION; IN VITRO STUDY; LIVER METABOLISM; LIVER MICROSOME; NORMAL HUMAN; PRIORITY JOURNAL; PROTEIN VARIANT; STEREOCHEMISTRY;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ARYL HYDROCARBON HYDROXYLASES; CELL LINE; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; HYDROXYLATION; IBUPROFEN; KINETICS; MICROSOMES, LIVER; STEREOISOMERISM; STEROID 16-ALPHA-HYDROXYLASE; STEROID HYDROXYLASES; SULFAPHENAZOLE;

EID: 0030857031     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00143-3     Document Type: Article

References (35)

1. Mills RFN, Adams SS, Cliffe EE, Dickinson W and Nicholson JS, The metabolism of ibuprofen. Xenobiotica 3: 589-598, 1973.
2. Rudy AC, Knight PM, Brater DC and Hall SD, Stereoselective metabolism of ibuprofen in humans. Administration of R-, S- and racemic ibuprofen. J Pharmacol Exp Ther 259: 1133-1139, 1991.
3. Rudy AC, Knight PM, Brater DC and Hall SD, Enantioselective disposition of ibuprofen in elderly persons with and without renal impairment. J Pharmacol Exp Ther 273: 88-93, 1995.
4. TB (CYP2C subfamily) in the actions of non-steroidal anti-inflammatory drugs. Drugs Exp Clin Res 19: 189-195, 1993.
5. Chen C-Y and Chen C-S, Stereoselective disposition of ibuprofen in patients with renal dysfunction. J Pharmacol Exp Ther 268: 590-594, 1994.
6. Adams SS, Bressloff P and Mason CG, Pharmacological differences between the optical isomers of ibuprofen: Evidence for the metabolic inversion of the (-)-isomer. J Pharm Pharmacol 28: 256-257, 1976.
7. Vane JR, Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nature New Biol 231: 232-235, 1971.
8. Kantor HS and Hampton M, Indomethacin in submicromolar concentrations inhibits cyclic AMP-dependent protein kinase. Nature 276: 841-842, 1978.
9. Abramson S, Korchak H, Ludewig R, Edelson H, Haines K, Levin RI, Herman R, Rider L, Kimmel S and Weissmann G, Modes of action of aspirin-like drugs. Proc Natl Acad Sci USA 82: 7227-7231, 1985.
10. Daikh BE, Lasker JM, Raucy JL and Koop DR, Regio- and stereoselective epoxidation of arachidonic acid by human cytochrome P450 2C8 and 2C9. J Pharmacol Exp Ther 271: 1427-1433, 1994.
11. Zeldin DC, DuBois RN, Falck JR and Capdevila JH, Molecular cloning, expression and characterization of an endogenous human cytochrome P450 arachidonic acid epoxygenase isoform. Arch Biochem Biophys 322: 76-86, 1995.
12. McGiff JC, Quilley CP and Carroll MA, The contribution of cytochrome P450-dependent arachidonate metabolites to integrated renal function. Steroids 58: 573-579, 1993.
13. Wrighton SA, VandenBranden M, Stevens JC, Shipley LA, Ring BJ, Rettie AE and Cashman JR, In vitro methods for assessing human hepatic drug metabolism: Their use in drug development. Drug Metab Rev 25: 453-484, 1993.
14. Gorski JC, Hall SD, Jones DR, VandenBranden M and Wrighton SA, Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol 47: 1643-1653, 1994.
15. Lowry OH, Rosebrough NJ, Farr AL and Randall RJ, Protein measurement with the Folin phenol reagent. J Biol Chem 193: 265-275, 1951.
16. Brooks CJW and Gilbert MT, Studies of urinary metabolites of 2-(4-isobutylphenyl)propionic acid by gas-liquid chromatography mass spectrometry. J Chromatogr 99: 541-551, 1974.
17. Rahman A, Korzekwa KR, Grogan J, Gonzalez FJ and Harris JW, Selective biotransformation of taxol to 6α-hydroxytaxol by human cytochrome P450 2C8. Cancer Res 54: 5543-5546, 1994.
18. Tassaneeyakul W, Birkett DJ, McManus ME, Tasseneeyakul W, Veronese ME, Andersson T, Tukey RH and Miners JO, Caffeine metabolism by human hepatic cytochromes P450: Contributions of 1A2, 2E1 and 3A isoforms. Biochem Pharmocol 47: 1767-1776, 1994.
19. Dirven HAAM, De Bruijn AAGM, Sessink PJM and Jongeneelen FJ, Determination of the cytochrome P450 IV marker, ω-hydroxylauric acid, by high-performance liquid chromatography and fluorimetric detection. J Chromatogr Biomed Appl 564: 266-271, 1991.
20. Segal IH, Enzyme Kinetics. John Wiley, New York, 1975.
21. Hall SD, Guengerich FP, Branch RA and Wilkinson GR, Characterization and inhibition of mephenytoin 4-hydroxylase activity in human liver microsomes. J Pharmacol Exp Ther 240: 216-222, 1987.
22. Rettie AE, Korzekwa KR, Kunze KL, Lawrence RF, Eddy AC, Aoyama T, Gelboin HV, Gonzalez FJ and Trager WF, Hydroxylation of warfarin by human cDNA-expressed cytochrome P450: A role for P-4502C9 in the etiology of (S)-warfarin-drug interactions. Chem Res Toxicol 5: 54-59, 1992.
23. Leo MA, Lasker JM, Raucy JL, Kim C-I, Black M and Lieber CS, Metabolism of retinol and retinoic acid by human liver cytochrome P45011C8. Arch Biochem Biophys 269: 305-312, 1989.
24. Hall SD, Hamman MA, Rettie AE, Wienkers LC, Trager WF, VandenBranden M and Wrighton SA, Relationships between the levels of cytochrome P4502C9 and its prototypic catalytic activities in human liver microsomes. Drug Metab Dispos 22: 975-978, 1994.
25. Kaiser DG, VanGiessen GJ, Reisecher RJ and Wechter WJ, Isomeric inversion of ibuprofen (R)-enantiomer in humans. J Pharm Sci 65: 269-273, 1976.
26. Lee EJD, Williams K, Day R, Graham G and Champion D, Stereoselective disposition of ibuprofen enantiomers in man. Br J Clin Pharmacol 19: 669-674, 1985.
27. Murray MD and Brater DC, Renal toxicity of the nonsteroidal anti-inflammatory drugs. Annu Rev Pharmacol Toxicol 33: 435-465, 1993.
28. Clive DM and Stoff JS, Renal syndromes associated with nonsteroidal antiinflammatory drugs. N Engl J Med 310: 563-572, 1984.
29. Veronese ME, Doecke CJ, Mackenzie PI, McManus ME, Miners JO, Rees DLP, Gasser R, Meyer UA and Birkett DJ, Site-directed mutation studies of human liver cytochrome P-450 isoenzymes in the CYP2C subfamily. Biochem J 289: 533-538, 1993.
30. Rettie AE, Wienkers LC, Gonzalez FJ, Trager WF and Korzekwa KR, Impaired (S)-warfarin metabolism catalyzed by the R144C allelic variant of CYP2C9. Pharmacogenetics 4: 39-42, 1994.
31. Sonnichsen DS, Liu Q, Schuetz EG, Schuetz JD, Pappo A and Relling MV, Variability in human cytochrome P450 paclitaxel metabolism. J Pharmacol Exp Ther 275: 566-575, 1995.
32. Wang S-L, Huang J-D, Lai M-D and Tsai J-J, Detection of CYP2C9 polymorphism based on the polymerase chain reaction in Chinese. Pharmacogenetics 5: 37-42, 1995.
33. 359 allelic variant in the tolbutamide polymorphism. Pharmacogenetics 6: 341-349, 1996.
34. Kaminsky LS, deMorais SMF, Faletto MB, Dunbar DA and Goldstein JA, Correlation of human cytochrome P4502C substrate specificities with primary structure: Warfarin as a probe. Mol Pharmacol 43: 234-239, 1993.
35. Spielberg S, McCrea J, Cribb A, Rushmore T, Waldman S, Bjornsson T, Lo M-W and Goldberg M, A mutation in CYP2C9 is responsible for decreased metabolism of Iosartan. Clin Pharmacol Ther 59: 215, 1996.